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The Synthesis of Novel Polycyclic Heterocyclic Ring Systems via Photocyclization. 12 . Benzo[ h ]naphtho‐[2′,1′:4,5]thieno[2,3‐ c ]quinoline and benzo[ f ]‐naphtho[2′,1′:4,5]thieno[2,3‐ c ]quinoline
Author(s) -
Luo JiannKuan,
Castle Steven L.,
Castle Raymond N.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300312
Subject(s) - quinoline , chemistry , ring (chemistry) , stereochemistry , polycyclic compound , nmr spectra database , medicinal chemistry , spectral line , molecule , organic chemistry , physics , astronomy
The synthesis of two previously unknown heterocyclic ring systems, namely benzo[ h ]naphtho[2′,1′:4,5]thi‐eno[2,3‐ c ]quinoline (1) and benzo[ f ]naphtho[2′,1:4,5]thieno[2,3‐ c ]quinoline (2) was accomplished via photocyclization of the appropriate amides followed by chlorination and catalytic dechlorination. The total assignment of 1 H and 13 C nmr spectra of 2 was determined utilizing two‐dimensional nmr methods, providing unequivocal structural proof of the two novel polycyclic ring systems.